2-Amino-4,5-dimethyl-1,3-thiazole → 3-(2-Methoxyethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine hydrobromide

HRID 78403

Reaction equation

HRID 78403 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:8])[S:5][C:6]=1[CH3:7].[CH3:9][O:10][CH2:11][CH2:12][Br:13]>>[BrH:13].[CH3:9][O:10][CH2:11][CH2:12][N:3]1[C:2]([CH3:1])=[C:6]([CH3:7])[S:5][C:4]1=[NH:8]

Participants

3

Reactant 2

HCID 732382-Amino-4,5-dimethyl-1,3-thiazoleHCID 809722-Bromoethyl methyl ether

Product 1

HCID 668517223-(2-Methoxyethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine hydrobromideYield 56%

Conditions

Temperature
85 °C

Procedure

A mixture of 4,5-dimethylthiazol-2-ylamine (9.0 g, 70 mmol) and 2-bromoethyl methyl ether (7.9 mL, 84 mmol) were heated at 85° C. for 12 hours. The mixture was cooled to ambient temperature and then triturated with isopropanol. The solid was collected by filtration and dried under vacuum to provide 10 g (56%) of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ ppm 2.17 (s, 3H), 2.19 (s, 3H), 3.25 (s, 3H) 3.56 (t, J=5.1 Hz, 2H) 4.16 (t, J=5.1 Hz, 2H) 9.41 (s, 1H); MS (DCI/NH3) m/z 129 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customtriturated with isopropanol
  3. filtrationThe solid was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6724b65297a84a548189d7aa4965c68e
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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